Aryl boronic acid-catalysed dehydrative substitution of benzylic alcohols for C-O bond formation
Abstract
A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C-O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the arylboronic acid and oxalic acid.
Citation
Estopiñá-Durán , S , Donnelly , L J , Mclean , E B , Hockin , B M , Slawin , A M Z & Taylor , J 2019 , ' Aryl boronic acid-catalysed dehydrative substitution of benzylic alcohols for C-O bond formation ' , Chemistry - A European Journal , vol. Early View . https://doi.org/10.1002/chem.201806057
Publication
Chemistry - A European Journal
Status
Peer reviewed
ISSN
0947-6539Type
Journal article
Description
We thank the University of St Andrews and the EPSRC for the award of a DTA studentship (S.E.-D.). We would also like to thank the EPSRC, University of St Andrews, and CRITICAT Centre for Doctoral Training for financial support [Ph.D. studentships to B.M.H, E.B.M and L.J.D; Grant code: EP/L016419/1]. J.E.T thanks the Leverhulme Trust for the award of an Early Career Fellowship (Grant code: ECF-2014-005).Collections
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